Gay Lost Bet Pegging Stories

11,553 results
Orientation
Length
Source
Infinite Scroll

You Bet Your Ass

by kudzu41999 on Aug 31, 2017
Gay Male

There's nothing worse than two divorced guys sitting around watching television on a Saturday night. Lamar lost everything when his wife took everything he owned. All he had left after he got home from work that day was the car and the clothes he had on his back. I wasn't much better off. The only difference seemed to be in the bills that were left behind. I...

The Collection

by thatkiwiguy on Sep 14, 2017
Gay Male

PLEASE NOTE: This is not really a romantic read. It's more a smutty tale touching slightly on themes of submission and control. It is a collection of scenes from a novel I'm working on and have pieced them together to be a shorter erotic tale. I hope you like it. ***** Callum Bradshaw carried a box of beer under his arm as he pressed the doorbell to his be...

Dominated By Daddy Ch. 01

by Redhead4Daddy on Sep 25, 2017
Gay Male

This is a work of fiction, I do not condone ANY of the activities portrayed in this story, nor do I recommend them to anyone. This story shares many similarities with my previous story "Steam Room Daddy" there are strong elements on non-consent in this story, so if that makes you uncomfortable this probably isn't the story for you. That being said, this stor...

Desert Heat

by rae121452 on Oct 15, 2017
Gay Male

I've been in this part of the Mid East for 20 years, first in the service and now as an employee of a company that contracts to the government. We work as guards and for the past 6 years we've been walking around carrying guns and guarding a neighborhood of bombed out houses from looters. Which is actually pretty funny. Unless someone discovers a thriving un...

Girlfriend's Bro Takes Charge Pt. 02

by somebody123 on Nov 12, 2019
Gay Male

The typically FIFA game is only five minutes, so it didn't take long for us to dive right into action. I placed my controller in my lap to cover up my flaccid cock, even though I was plenty proud of it. Despite what Ayden had said, I knew that my dick was average and felt confident that I was much bigger than this teenager who was eight years younger than me...

Our Bath

by Elected on May 14, 2019
Gay Male

"Whew! What a run, huh, buddy?" Lee swung his arm around my shoulder. Immediately I felt the sticky heat from his arm soak my neck, and I recoiled. "Lee, quit it! You're all sweaty!" "What are you so worked up about?" Lee laughed, giving my shoulder a squeeze and pulling me tighter to his body. I wriggled and squirmed, getting myself free and shooting him...

The Handyman Ch. 06

by Bjsroxxs on Jul 6, 2020
Gay Male

"How do I look?" asked Matthew before he stepped into my truck. He wore a light blue polo shirt with blue skinny jeans. I had told him to wear something casual. Which he did. "Looks great," I said. Matthew opened the door and hopped into the truck. We had gotten used to not kissing in front of his house. For fear either his mom or neighbors would see. With...

A Challenge Ch. 02

by drmweaver705 on Jun 15, 2020
Gay Male

All characters are over 18. ***** FRIDAY NIGHT "So, who won that challenge?" Anton asked Dylan. The challenge was simple. Anton, a very out gay man, had boasted of a recent conquest in which he made a nominally straight man shoot his load six times in one evening. The audience for Anton's story was his straight friend, Dylan. The younger man scoffed at A...

If Motel Rooms Could Talk

by timmywells on Aug 18, 2017
Gay Male

The dingy and dated decor of The Skylane Motel on Central Avenue just outside the state's capital city hadn't been updated since Gerald Ford was President, but most of the people who stayed there didn't care. That was the case on the night of May 25th, when a nondescript 53 year old married man named Melvin Stark paid the $33.50 to rent room 108. The man ha...

My First Glory Hole Experience

by Kent100 on Sep 14, 2017
Gay Male

When I was 34, I was a very happily married full fledged heterosexual man. My wife was a very attractive blonde, several years my junior and our bedroom activities were really hot. I considered myself 100% straight, even though I had received a drunken blow job from my college dorm roommate, when I was 18, which I did not return the favor on by the way. It w...